


The Mini Skirt Problem

by BloodyCreaturePosterGirl



Series: Wardrobe Malfunction [2]
Category: Supernatural
Genre: F/M, Reader-Insert
Language: English
Status: Completed
Published: 2016-06-18
Updated: 2016-06-18
Packaged: 2018-07-15 21:06:06
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,198
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7238473
Author URL: https://archiveofourown.org/users/BloodyCreaturePosterGirl/pseuds/BloodyCreaturePosterGirl
Summary: <blockquote class="userstuff">
              <p>Dean's brilliant idea turns against him.</p>
            </blockquote>





	The Mini Skirt Problem

**Author's Note:**

> This is but isn't a sequel to Little Blue Dress.

“You want me to…what?” Y/N hissed through her teeth. She was glaring across the table at both Sam and Dean Winchester who had ask her to step out of her comfort zone and into a mini skirt before her first sip of coffee in the morning. Y/N had been a tomboy her entire life, even back when her mother desperately tried to make her girly by forcing dresses on her. Sam and Dean knew that. They knew the last time she had probably worn a skirt had been when she was eight years old… but they asked her anyway.   
“We… were hoping you would be willing to draw this guy out,” Sam tried a different approach, knowing full well that he was walking the edge of a knife. Things like skirts and dresses make Y/N uncomfortable because she was uncomfortable with showing off skin. Skirts were a vulnerable thing.   
“By wearing a mini skirt?” she asked incredulously, the pitch of her voice rising.   
“He may be a werewolf, but he certainly knows how to appreciate a woman in a sexy outfit,” Dean grinned.   
“Real helpful, Dean,” Sam said with a roll of his eyes.   
“What?” Dean asked with a shrug of his shoulders. “What hot blooded male doesn’t love a woman in a mini skirt?”   
Y/N worried her bottom lip between her teeth. “Are you sure that this will work?”   
Sam and Dean turned hopeful eyes to Y/N. “You’ll do it?” They asked in unison.   
“You won’t… make fun of me?”   
“Of course not!”   
Several hours and a trip to the local mall later Y/N was nervously staring at her refection in the bathroom mirror. She had agreed out of her desire to help the brothers with this new case. She hadn’t been out on a case in weeks due to an injury from the last case and she had been itching to get back out on the road. But now, as she stood in the too tight top and the too tiny mini she wasn’t so sure this was a good idea.   
The top was a dark burgundy that hugged her curves and dipped low in the front to give more than a teasing view of her ample cleavage. Though it was lower cut that she would typically wear, Y/N found she quite liked it. The mini on the other hand… she wasn’t comfortable in. It was black with gray and burgundy paid strips that reminded her a little too much of the tiny schoolgirl outfits that came out around Halloween. True to that ideal, the skirt sat low on her hips and was hardly long enough to cover her ass. Y/N turned her backside to the mirror to make sure that her black lace panties could not be seen.   
A soft knock sounded against the door, making her jump.   
“Y/N?” Dean’s voice called through the door. “You about ready?”   
Y/N double-checked her soft curls and red lips in the mirror as she slipped into the heels Sam had convinced her to get as well before slowly pulling open the door. “Yeah, sorry I took so long,” she mumbled, not meeting Dean’s eyes.   
Y/N fiddled nervously with the hem of her skirt, as if tugging at it might make it grow a few more inches. Her other hand pressed flat against her stomach in hopes of steadying the flutter within at the thought of Dean Winchester seeing her in such an outfit. Would he approve?   
“How… how do I look?” She asked timidly, looking up at Dean through her lashes.   
Dean stood frozen in place. He had always thought Y/N was a beautiful woman and had always loved her company, more often than not being the first to suggest she come along with the brothers on one case or another. But, in all the time the Winchesters had known Y/N he had never seen her like this. All dolled up in a tiny mini skirt, heels accentuating her long, long legs. Red suited her in an indescribable way, making her skin glow like fine porcelain and her cheeks flush… or perhaps her cheeks were flushed with a blush… either way, Dean was enthralled.   
All at once Dean was bombarded with the strong desire to pull her soft body flush against his and kiss her senseless. To feel the heat of her bare skin against his, her hair a halo of curls splayed across his pillows, to hear her soft sweet voice call his name in ecstasy.   
“Dean?” She called softly, waking him from his thoughts.   
His lips formed the response before he even realized she’d asked him a question. “You look incredible.” His tone was breathless and it earned him a shy smile that made his heart squeeze within his chest.   
“Thank you,” she murmured. “I confess I’m extremely nervous.”   
Dean’s brows pulled together in confusion. “Why?”   
“Why?” Y/N echoed with a laugh. “Because I’ve never worn anything like this in public before… let alone with the intention of gaining a man’s attention.”   
Dean’s blood froze within his veins, her words echoing through his mind like the press of a blade through flesh. Gain a man’s attention? She didn’t need to gain another man’s attention… not when she had his fully. Dean was about to voice that exact thought when Sam rounded the corner looking for the two of them.   
“Dean is Y/N—whoa…” Sam stopped dead in his tracks, mouth-hanging open fractionally.   
“She isn’t goin’,” Dean all but growled. He did not approve of the way his brother was staring at her long, long legs. He didn’t approve of anyone else seeing her in so little if he were being perfectly honest. She was not some sleazy little bar skank.   
“What?” Sam and Y/N asked in unison.   
“Y/N, you didn’t even wanna do this in the first place,” Dean said defensively.   
Y/N smiled, albeit confused. “But I agreed. I want to help, Dean.”   
“Dude, what’s the big deal? This was your idea,” Sam asked with a raised eyebrow.   
“We can’t make her do this for the sake of a case,” Dean said, crossing his arms over his chest.   
“Dean—”  
“Sam, she ain’t doin’ it.”  
“Dean,” Y/N said softly, laying a small hand over his forearm. “It’s okay, I can do this. Besides, it’ll be over before we know it. I’ll be okay.”   
Dean subtly relaxed, but it didn’t not go unnoticed.   
Sam watched the two interact and sudden realization dawned on the younger Winchester. Dean had feelings for Y/N. They hadn’t even made it to the bar and he was already jealous at the thought of other men checking her out. Sam snickered drawing Dean’s and Y/N’s attention away from one another.   
“No need to be jealous, bro,” Sam said with a grin.   
Dean shot Sam a dirty look.   
“Jealous?” Y/N echoed in confusion. “I could always lead him to you and you can gank him yourself if it really means that much to you.”   
Sam snorted with laughter as Dean dragged a hand over his face, completely flabbergasted that she would believe he was jealous that she might get the kill. He didn’t give a damn who got the kill! The leering stares of drunken assholes in the bar who thought she was up for grabs is what made his blood boil. Because she wasn’t taken and it was perfectly reasonable and not at all out of the question that she might take interest in someone else. Because Y/N wasn’t his no matter how badly he wished she was.   
“Fine. Whatever. Lets just get it over with,” he grumbled.   
Sam and Y/N lead the way out of their motel room shortly after, Y/N shooting confused looks in Dean’s direction the entire walk to the bar, but he refused to acknowledge it. He wasn’t about to ruin whatever they had with his newly realized feelings.   
Sam and Dean had gone into the bar ahead of Y/N to scout the place and make sure their mark was there. Clocking the man sitting on a barstool on the far left hand side Sam called Y/N, who answered in the first ring. “You ready?” he asked.   
“As I’ll ever be,” she said with a laugh, dragging in a deep breath, righting her outfit, and heading through the door. When Y/N stepped through the door she instantly scanned the place, finding Sam and Dean in seconds.   
“Alright. He’s the one at the end of the bar, on the left hand side, do you see him?”   
Y/N scanned the bar to find a not entirely unattractive man sitting on the last barstool on the left hand side. He was hunched in on himself, clearly wanting to be left alone, and to Y/N’s luck, the only open barstool left was the one right beside him. “I see him,” she confirmed.   
“We’ll be right here the whole time. If you need anything, I mean it sweetheart, if you need anything. If this guy creeps you out too much, if he gets all touchy feely… I’ll—we’ll be there in a flash.” Y/N smiled despite herself at the sound of Dean’s voice on the other end of the call.   
“I know, Dean,” she said softly. “Time to get this show on the road.”   
Dean’s brows knit together at the sigh in her voice. What did she mean by show? As if on cue, Y/N, in her teeny tiny mini skirt and heels, strut past their table without so much as a glance in their direction. Dean’s lips parted in surprise, his green eyes trailing after her. She held herself at her full height, still not taller than him in those sky-high heels, her every step confident. Dean’s eyes roamed up her legs to the sway of that tiny skirt with the sexy swing of her hips.   
“You’re drooling,” Sam snickered.   
Dean shot a glare at Sam from across the table, kicking his brother in the shin. Without saying a word Dean turned back to track Y/N, his hands balling into fists when he noticed all the stares she was getting. He definitely regretted letting her leave their motel in that tiny little outfit.   
Determined not to let his feelings get the better of him on a case, Dean tried to push down the jealousy he felt and watched for telling signs that Y/N might need help. She had perched herself on the stool next to their target without even a glance in his direction, but her tiny outfit had drawn his the moment she was within range. Their mark was talking to her before the glass of whisky she had ordered had even touched to coaster in front of her.   
The music inside the bar was far too loud for the brothers to hear any of the conversation Y/N was having with their mark, but she was playing her role well. Anything seemingly funny the man said she would tip her head back and laugh as though she genuinely found him funny. From where they sat, Sam and Dean could only see the side of her face unless she turned to face their guy, but even from a profile Dean could see the color fill her cheeks whenever the man complimented her.   
Sam watched his brother from across the table, amused and surprised at how well his brother was keeping himself in check… if you looked past the glares he shot at every man to so much as look in Y/N’s general direction. Or the clenching an unclenching of his hand around his beer, or the tick of a muscle along his jaw. Dean was radiating jealousy like a scorned lover. Sam found it brilliant.   
Suddenly the glass in Dean’s hand shattered causing Sam to jump, his head snapping in Y/N’s direction to see what had caused such a reaction out of Dean. At the bar, their target had decided to become overly friendly with Y/N, his eyes glued to her chest as he slid his fingers up the length of her bare thigh.   
“Dean…” Sam warned. He didn’t like to see the guy feeling his best friend up either, but Dean couldn’t blow their cover. Not now.   
Both brothers watch Y/N as she gave the man a tight smile, stopping his hand before it could tail any further up. Grasping the man’s hand she leaned forward to whisper something in his ear before leading the back toward the back of the bar, the man trailing behind like a dog who just got the bone.   
Dean stood from his chair the moment the door of the bar closed behind Y/N and their mark, nearly knocking the table over in the process.   
“Dean… Y/N is capable of taking care of this guy on her own... don’t blow her cover,” Sam tried to sooth his brother.   
“Does it look like I give a damn?” Dean snapped, turning his murderous glare at his brother. “The fucker touched her. I’m going to kill him.”   
Sam did not try to stop him as he stormed out of the bar, not even seeing the cute little waitress that had tried to get his attention. Sam sighed, slouched back in his chair, and ordered another beer from the dejected waitress. He had no intention of getting between his brother and Y/N, he’d just head back to the motel when he finished he beer.   
Outside the bar Dean came to a haut, waiting for the door to slam shut behind him and listening for Y/N’s voice to figure out which way she had lead the prick. The pop of a pistol rang loud and clear from around the side of the bar, closest to the woods that lined the road. Dean headed in that direction without a second though, withdrawing the pistol he had touched into the back of his jeans.   
Dean rounded the corner to find their mark pressed against the wall, his hands in the air in defense, and the barrel of Y/N’s pistol pointed directly between the man’s eyes. Blood bloomed red against the crisp while of the man’s shirt where Y/N had shot him in the shoulder. Dean grinned, that’s my girl, he thought proudly.   
“I should have killed you when I had the chance,” the man spat at Y/N.   
“Yes, you should have,” she agreed, tilting her head in Dean’s direction as a way of letting him know she was aware of his presence.   
The werewolf’s head snapped in Dean’s direction and he growled, low and utterly inhuman. “Who the fuck are you?” he snapped.   
“The man who’s going to put a silver slug between your eyes for even thinking of touching my girl,” Dean remarked coolly, pleased with the color that flooded Y/N’s cheeks.   
The werewolf snorted and again it was utterly inhuman. “What kind of man lets his little bitch hang all over other men?”  
“Says the fucking creep who said and I quote, “its okay if you have a boyfriend, baby, what he doesn’t know won’t hurt him”,” Y/N snapped.   
The werewolf shrugged as if he couldn’t be bothered.  
“You told him you had a boyfriend?” Dean asked in surprise.   
Y/N flushed but nodded her head nonetheless.   
“Were you thinkin’ of me?” Dean asked.   
The werewolf groaned and Y/N’s lips parted in surprise, stumbling over her words as she tried to answer him. “I-I m-might have been… what’s it t-to you Winchester?”   
“Winchester?” The werewolf growled in recognition.   
“Dean, to be more specific,” Dean agreed.   
“Son of a bitch…” The werewolf bemoaned. “Look man, I was just looking to get laid, I can’t help it if your girl came onto me.”   
“Dream on, you creep. Don’t even pretend you hadn’t intended to rip my chest cavity open and tear out my heart,” Y/N said with a roll of her eyes.   
“Not until after I had you howling at the moon,” the werewolf said with a wink. “I’m not a necrophiliac, doll.”  
Y/N gave the man a look of complete disgust.   
“You ain’t gettin’ lucky with my girl,” Dean growled.   
Y/N’s eyes snapped back to Dean, so surprised by the seriousness in his voice that she missed the werewolf’s fingers reaching for her. Dean opened his mouth to threaten the bastard for even thinking he could touch her when gunfire filled the air. The second the man’s fingertips had touched Y/N’s ribs she had pulled the trigger, sending a silver slug right between his eyes, and taking the joy of killing him from Dean. Y/N hadn’t even batted a lash as she’d pulled the trigger and Dean smirked. Y/N was the sexiest huntress he’d ever had the pleasure of meeting.   
Barrel still smoking she lowered her pistol, not once glancing down at the dead man at her feet as she stepped closer to Dean. Dean smiled proudly at her until her step faulted and her cheeks suddenly flushed alit with color and her eyes dropped from his.   
Dean’s smiled dropped instantly, his heart clouding with worry. “Hey, you okay, sweetheart? He didn’t hurt you… did he?”   
Y/N shook her head still not meeting Dean’s eye. “No…I-I’m sorry,” she stuttered. “I… I just feel so exposed.”   
A smirk tugged at the corner of Dean’s mouth as he allowed his eyes to roam over her pleasing figure once more, without the jealous fueled anger of knowing others were going to see her in that tiny outfit to sour his mood. Even in the moonlit alley, she was incredible.   
“I like it,” Dean said firmly.   
Y/N’s eyes grew wide, finally meeting Dean’s again as she searched his face for any trace of a lie. “You…do?” she asked timidly.   
Dean stalked closer to her, his arm snaking around her waist and pulling her body flush against his so that she could feel the evidence of his desire for her. “Yes,” he mumbled, lips ghosting over her neck.   
Y/N’s lips parted on a breathy sigh. “I feel naked wearing so little.”   
“I’d love to see you naked… naked and moaning in pleasure for me,” Dean countered.   
She gasped as his teeth grazed over her jaw, his tongue flicking out to tease the corner of her mouth. “I-I should wear skirts more often.” If this is how Dean reacted to her wearing mini skirts, she could definitely get used to wearing them more often.  
“You’re sexy in anything you wear, sweetheart,” Dean cooed. “But, yes, you should wear this more often. For me only, in the privacy of our room,” he growled, hiking her legs up around his waist and walked her toward their motel. Sammy was more than welcome to have their room all to himself, Dean would be spending the night in Y/N’s room… and every night that followed so long as she permitted it. By the needy moan and the roll of her hips against his own, Dean had no doubts that this would continue.


End file.
